The group was influenced to some extent by American rap and gangsta rap music, especially Tupac Shakur, and the "gangsta" culture portrayed therein.[2][3][4] Since the title 'West Side Niggaz' would have been an entirely unacceptable phrase to be regularly used on news programmes concerning the group, the title was amended to render it to the innocuous 'West Side Boys'. Prior to their destruction, the group's size had expanded to around 600 but later suffered about 200 defections.[1]

At the time that the West Side Boys were active, large areas of Sierra Leone were controlled by militias. However, there existed no provable connections to the main rebel group in Sierra Leone, the Revolutionary United Front.

Frequently the subject of British media, due in part to their kidnapping of British soldiers and their flamboyant character, as reported by the BBC: "They were known for wearing bizarre clothing – women's wigs and flip-flops were favourites – and being almost perpetually drunk."[5]

A 2008 article published in the Journal of Modern African Studies offers an alternative view of the West Side Boys as an effective military unit employing military and political techniques to achieve defined goals, as opposed to a criminal gang with no political purpose engendered by the perpetual lawlessness and social breakdown of the country.[6]